Compounds > 8-ethoxy-2-(4-fluorophenyl)-3-nitro-2h-chromene
Page last updated: 2024-11-09

8-ethoxy-2-(4-fluorophenyl)-3-nitro-2h-chromene

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Description

8-ethoxy-2-(4-fluorophenyl)-3-nitro-2H-chromene: an antineoplastic agent that inhibits the expression of cyclins D1, D2, and D3 and arrests cells at the G0/G1 phase [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID2732983
CHEMBL ID2385162
SCHEMBL ID16602977
MeSH IDM0556360

Synonyms (12)

Synonym
OPREA1_688829
8-ethoxy-2-(4-fluorophenyl)-3-nitro-2h-chromene
S14161 ,
CHEMBL2385162
cyto9g10
883046-50-2
SCHEMBL16602977
CCG-249194
8-ethoxy-2-(4-fluorophenyl)3-nitro-2h-chromene
s14161, >=98% (hplc)
NCGC00387684-01
AKOS040755040

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Comparable studies showed that S14161 has a higher potential bioavailability than LY294002, a prototypical inhibitor of pan-class I PI3K."( Modulation of platelet activation and thrombus formation using a pan-PI3K inhibitor S14161.
He, S; Hu, H; Li, Q; Liu, X; Mao, X; Ren, L; Shen, J; Wang, Q; Wu, Q; Yi, W; Zhu, L, 2014)		0.4
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)		0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID749216Growth inhibition of human HeLa cells at 20 uM after 24 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749228Cytotoxicity against mouse B16 cells after 24 to 72 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749227Cytotoxicity against human U87 cells after 24 to 72 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749231Cytotoxicity against human K562 cells after 24 to 72 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749205Induction of apoptosis in human A549 cells assessed as activation of caspase-3 at 10 uM2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID1339036Inhibition of collagen-induced platelet aggregation in human platelet rich plasma preincubated for 10 mins followed by collagen addition by aggregometric method
AID749218Growth inhibition of human A549 cells at 5 to 20 uM after 24 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749229Cytotoxicity against human MDA-MB-231 cells after 24 to 72 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749224Growth inhibition of human H47D cells at 20 uM after 72 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749225Growth inhibition of human SKOV3 cells at 20 uM after 72 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749211Inhibition of PI3K in human HeLa cells assessed as inhibition of EGF1-induced AKT phosphorylation up to 20 uM after 24 hrs by Western blot analysis2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749222Growth inhibition of human HeLa cells at 20 uM after 72 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749223Growth inhibition of human A549 cells at 20 uM after 72 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749221Growth inhibition of human H460 cells at 20 uM after 72 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749220Growth inhibition of human SPCA1 cells at 20 uM after 72 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749226Growth inhibition of human PC3 cells at 20 uM after 72 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749230Cytotoxicity against human LP-1 cells after 24 to 72 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749217Growth inhibition of human HeLa cells at 5 uM after 24 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749212Inhibition of PI3K in human SKOV3 cells assessed as inhibition of EGF1-induced AKT phosphorylation up to 20 uM after 24 hrs by Western blot analysis2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID749213Antiangiogenic activity in HUVEC assessed as inhibition of cell migration by measuring area of wounded gap at 5 uM after 8 to 24 hrs by wound healing assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's8 (100.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.31

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.31 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.31)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
triethylenediamine
triethylenediamine: RN given refers to parent cpd. triethylenediamine : An organic heterobicylic compound that is piperazine with an ethane-1,2-diyl group forming a bridge between N1 and N4. It is typically used as a catalyst in polymerization reactions.		2.0810bridged compound;
diamine;
saturated organic heterobicyclic parent;
tertiary amino compound		antioxidant;
catalyst;
reagent
arsenic trioxide
Arsenic Trioxide: An inorganic compound with the chemical formula As2O3 that is used for the treatment of ACUTE PROMYELOCYTIC LEUKEMIA in patients who have relapsed from, or are resistant to, conventional drug therapy.		2.1110
proline
Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.		2.0810amino acid zwitterion;
glutamine family amino acid;
L-alpha-amino acid;
proline;
proteinogenic amino acid		algal metabolite;
compatible osmolytes;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
bortezomib
[no description available]		2.1110amino acid amide;
L-phenylalanine derivative;
pyrazines		antineoplastic agent;
antiprotozoal drug;
protease inhibitor;
proteasome inhibitor
melphalan
Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.		2.1110L-phenylalanine derivative;
nitrogen mustard;
non-proteinogenic L-alpha-amino acid;
organochlorine compound		alkylating agent;
antineoplastic agent;
carcinogenic agent;
drug allergen;
immunosuppressive agent
arsenic
Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)		2.1110metalloid atom;
pnictogen		micronutrient
ConditionIndicatedRelationship StrengthStudiesTrials
Hematologic Malignancies
[description not available]		02.1510
Leucocythaemia
[description not available]		02.520
Kahler Disease
[description not available]		03.0240
Leukemia
A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)		02.520
Multiple Myeloma
A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.		03.0240
Hematologic Neoplasms
Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.		02.1510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.110
Blood Clot
[description not available]		02.110
Thrombosis
Formation and development of a thrombus or blood clot in the blood vessel.		02.110
Adenoma Sebaceum
Facial ANGIOFIBROMA in tuberous sclerosis		02.1110
Tuberous Sclerosis
Autosomal dominant neurocutaneous syndrome classically characterized by MENTAL RETARDATION; EPILEPSY; and skin lesions (e.g., adenoma sebaceum and hypomelanotic macules). There is, however, considerable heterogeneity in the neurologic manifestations. It is also associated with cortical tuber and HAMARTOMAS formation throughout the body, especially the heart, kidneys, and eyes. Mutations in two loci TSC1 and TSC2 that encode hamartin and tuberin, respectively, are associated with the disease.		02.1110